


Dean's Princess

by noyindesu



Category: Supernatural
Genre: Bottom Sam, Crossdressing, Curvy Sam, Feminine Sam, M/M, Perverted!Dean, Short Sam, Short Sam Winchester, Top Dean, Virgin!Sam, Wincest - Freeform
Language: English
Status: Completed
Published: 2017-01-22
Updated: 2017-01-22
Packaged: 2018-09-19 04:30:36
Rating: Mature
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 764
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9418829
Author URL: https://archiveofourown.org/users/noyindesu/pseuds/noyindesu
Summary: Sam tries on a dress and dean walks in on him. He likes what he sees





	

**Author's Note:**

> Sam's Outfit: https://ae01.alicdn.com/kf/HTB1NuxsIXXXXXcgXFXXq6xXFXXXX/2014-New-Fashion-Women-s-Cute-font-b-Japanese-b-font-Sailor-Navy-Striped-Chiffon-font.jpg

Sam stares at himself in his mirror. Looking at the cute bow tie on his chest, he tugs at it a bit and smiles and twirls around. The skirt flaring up as he spins. Sam thinks the outfit is adorable. "oh wow sam, what's with the dress?" Dean snickered. Sam's face heated up and he ran over to Dean and started punching him in his arm.

"Dean stop coming in my room without knocking first!" He started to get pissed. He was embarrassed, his older brother saw him being his girly self. "hey Sammy I won't say anything!" Dean laughed. Sam turned around and crossed his arms. Dean smirked and grabbed the tip of Sammy's skirt and raised it up, looking at sam's teddy bear panties. "Oooh! Even comes with cute panties!" Dean gulped and giggled. Sam blushed deeply and slapped Dean in his face, creating a red mark. "Y-You Jerk! Get out my room!" Sam yelled with tears in his eyes and pushed dean out his room and slammed his door. Dean felt bad but he knew it was worth it, he rubbed his cheek where Sam slapped him. 

Sam sat on his bed and wiped his eyes with his arm. "Dean is a jerk..' Sam started to cry again, quietly. Dean was still standing at sam's door, he heard sam crying. "Sammy? Are you okay?" He asked from outside. "I'm okay..' Sam wiped his eyes and walked over to the door and opened it, looking up at his taller brother. "Pick me up..." Sam demanded. Dean picked sam up, bridal style of course. Sam grabbed Dean's cheeks and turned his head to face his. Dean loved the touch of Sammy's soft hands. He started at sam's lips also, he wanted to kiss them, they look soft as hell. Sam blushed and kissed Dean's cheek where he slapped him at. "I'm sorry for slapping you..." Sam apologized. Dean blushed again and nodded. "it's fine" 

Sam kissed dean with softly and jumped out of his arms and ran into his room shutting the door. Dean had a little celebration in the hallway. Come to think of it Sam was a virgin so if they had sex, dean would be his first. Dean busted into sams room and ran over to his bed then pulled sam over and put him on top of his crotch. "D-Dean Oh my GOD." Sam blushed. He didn't mind sitting on Dean. He could feel dean's member against him. He blushed red. "You okay Sammy?" Dean asked. Sam nodded. Dean picked up sam and put him on the bed and got on top of him, he kissed sam's neck and went down to his shoulder. Sam's breathing started to hitch. "Sammy, you're already out of breath?" Dean asked as he sat up on his knees and started to take off his shirt and unbutton his pants. "We haven't even started the fun part yet!~" Dean's member popped out of his pants. Sam gulped and was slightly frightened by how big it was. Dean raised Sam's skirt up and moved sam's panties off. He placed his member at Sam's entrance. Sam gasps and moans softly. "Sammy im not even in you yet!~ You really are a virgin!" He pushed himself in Sam, just a bit so it wouldn't hurt him. Sam's legs started shaking and he moaned out. "D-D-Deannnn!" He cried out. "That hurts!" 

"I'm sorry princess" Dean giggles and pushed himself in all the way. Sam was moaning and groaning. "D-Don't move...~" Sam has tears in his eyes, he was hurting but he didn't care. "R-Ready?" Dean asked. Sam nodded. Dean started thrusting in and out of sam. Sam was out of breath and was moaning more. Sam grabbed onto the bed sheets and cried out with tears going down his cheek. "T-This hurts..!" He cried. Dean kept going completely ignoring sam. He thrust harder and faster, They both moaned, the moans mixed with pain and pleasure. Sam moaned loudly, loud enough for people outside to hear. Dean went harder and he came inside sam. Sam on the other hand was crying and shaking. "Dean! That Hurt!!" Sam yelled. He was weak. He pushed Dean off of him and sat up and turned the other way. He knew he couldn't walk so he didn't try. "Y-You're mean! Get out my room!" Sam pushed him off his bed and got under his blankets. 

Dean giggled. "Sorry baby i'll be careful next time~" He kissed Sam's neck and walked out his room,shutting the door behind him. 

Dean was proud of himself.


End file.
